tert-Butyl piperazine-1-carboxylate → HCID 15521018, compound

HRID 651091Notes

Reaction equation

HRID 651091 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19]([C:24]([NH:26][CH:27]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:28](O)=[O:29])=[O:25])=[CH:18]2>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:28](=[O:29])[CH:27]([NH:26][C:24]([C:19]2[NH:20][C:21]3[C:17]([CH:18]=2)=[CH:16][C:15]([Cl:14])=[CH:23][CH:22]=3)=[O:25])[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 155210162-[(5-Chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid

Product 1

HCID 15521018HCID 15521018, compound

Procedure

1-Piperazinecarboxylic acid t-butyl ester (1.2 mmol) and 2-[(5chloro-1H-indole-2-carbonyl)-amino]-3-phenyl-propionic acid (0.6 mmol) were coupled according to procedure A (0-25° C. reaction temperature, reaction time 4 days, extraction with acid first, then base), and the crude product purified by column chromatography on silica gel eluted with 30% ethyl acetate in hexanes to give a colorless foam: Yield 290 mg, 95%; HPLC (70/30) 6.23 min (99%); PBMS 512/514 (MH+, 100%);

Workup

  1. custom0-25° C. reaction temperature, reaction time 4 days, extraction with acid first
  2. custombase), and the crude product purified by column chromatography on silica gel
  3. washeluted with 30% ethyl acetate in hexanes
  4. customto give a colorless foam

Sources & evidence

ORD record
ord-edc08a7e5254482e8c20df86308ae258
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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